# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd16133
_database_code_depnum_ccdc_archive 'CCDC 1473530'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H28 F N O3 S'
_chemical_formula_weight         417.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.6209(17)
_cell_length_b                   10.0531(16)
_cell_length_c                   10.7441(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.548(4)
_cell_angle_gamma                90
_cell_volume                     1137.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2046
_cell_measurement_theta_min      5.572
_cell_measurement_theta_max      41.589

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6578
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             4070
_reflns_number_gt                3566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.927

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.1889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.04(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4070
_refine_ls_number_parameters     289
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66103(9) 0.97847(10) 0.40628(8) 0.0503(3) Uani 1 1 d . . . . .
F1 F 0.3804(2) 0.8259(2) 0.5724(2) 0.0623(7) Uani 1 1 d . . . . .
N1 N 0.6128(4) 0.9241(4) 0.5357(4) 0.0605(10) Uani 1 1 d . . . . .
O1 O 0.3498(4) 1.1243(3) 0.4036(3) 0.0731(10) Uani 1 1 d . . . . .
O2 O 0.3001(5) 0.9125(4) 0.3568(4) 0.1001(14) Uani 1 1 d D . . . .
O3 O 0.6460(3) 0.8678(4) 0.3150(3) 0.0700(9) Uani 1 1 d . . . . .
C1 C 0.0402(5) 0.9451(7) 0.8285(5) 0.0877(18) Uani 1 1 d . . . . .
H1 H 0.0323 0.8560 0.8056 0.105 Uiso 1 1 calc R U . . .
C2 C -0.0472(6) 1.0018(10) 0.8979(6) 0.108(2) Uani 1 1 d . . . . .
H2 H -0.1138 0.9513 0.9209 0.129 Uiso 1 1 calc R U . . .
C3 C -0.0346(7) 1.1321(10) 0.9320(7) 0.112(2) Uani 1 1 d . . . . .
H3 H -0.0929 1.1706 0.9785 0.134 Uiso 1 1 calc R U . . .
C4 C 0.0624(6) 1.2060(8) 0.8985(6) 0.102(2) Uani 1 1 d . . . . .
H4 H 0.0702 1.2949 0.9222 0.123 Uiso 1 1 calc R U . . .
C5 C 0.1496(5) 1.1499(6) 0.8292(5) 0.0762(14) Uani 1 1 d . . . . .
H5 H 0.2160 1.2013 0.8070 0.091 Uiso 1 1 calc R U . . .
C6 C 0.1393(4) 1.0200(5) 0.7931(4) 0.0607(12) Uani 1 1 d . . . . .
C7 C 0.2256(4) 0.9599(5) 0.7130(4) 0.0602(11) Uani 1 1 d . . . . .
H7 H 0.2267 0.8675 0.7085 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3016(4) 1.0249(4) 0.6470(3) 0.0483(10) Uani 1 1 d . . . . .
H8 H 0.3009 1.1172 0.6517 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3887(4) 0.9631(4) 0.5653(4) 0.0515(9) Uani 1 1 d . . . . .
C10 C 0.5288(4) 1.0016(4) 0.6047(3) 0.0445(9) Uani 1 1 d . . . . .
H10 H 0.5383 1.0953 0.5827 0.053 Uiso 1 1 calc R U . . .
C11 C 0.5648(3) 0.9890(5) 0.7451(3) 0.0476(8) Uani 1 1 d . . . . .
C12 C 0.5668(5) 1.0994(5) 0.8200(5) 0.0651(13) Uani 1 1 d . . . . .
H12 H 0.5486 1.1822 0.7834 0.078 Uiso 1 1 calc R U . . .
C13 C 0.5952(6) 1.0902(7) 0.9477(5) 0.0835(18) Uani 1 1 d . . . . .
H13 H 0.5975 1.1665 0.9970 0.100 Uiso 1 1 calc R U . . .
C14 C 0.6205(5) 0.9672(8) 1.0034(4) 0.0793(15) Uani 1 1 d . . . . .
H14 H 0.6386 0.9601 1.0902 0.095 Uiso 1 1 calc R U . . .
C15 C 0.6185(5) 0.8585(6) 0.9310(5) 0.0749(15) Uani 1 1 d . . . . .
H15 H 0.6362 0.7758 0.9681 0.090 Uiso 1 1 calc R U . . .
C16 C 0.5903(5) 0.8676(5) 0.8011(4) 0.0609(12) Uani 1 1 d . . . . .
H16 H 0.5888 0.7913 0.7521 0.073 Uiso 1 1 calc R U . . .
C17 C 0.3447(4) 1.0089(5) 0.4305(4) 0.0598(11) Uani 1 1 d . . . . .
C18 C 0.242(2) 0.9394(19) 0.2253(16) 0.120(4) Uani 0.6 1 d D U P A 1
H18A H 0.1865 0.8653 0.1972 0.143 Uiso 0.6 1 calc R U P A 1
H18B H 0.1885 1.0179 0.2256 0.143 Uiso 0.6 1 calc R U P A 1
C19 C 0.3231(19) 0.958(2) 0.1411(12) 0.117(3) Uani 0.6 1 d D U P A 1
H19A H 0.3831 1.0262 0.1709 0.176 Uiso 0.6 1 calc R U P A 1
H19B H 0.2770 0.9850 0.0623 0.176 Uiso 0.6 1 calc R U P A 1
H19C H 0.3675 0.8767 0.1301 0.176 Uiso 0.6 1 calc R U P A 1
C18' C 0.222(3) 0.976(3) 0.238(2) 0.118(4) Uani 0.4 1 d D U P A 2
H18C H 0.1571 0.9179 0.1948 0.142 Uiso 0.4 1 calc R U P A 2
H18D H 0.1878 1.0634 0.2517 0.142 Uiso 0.4 1 calc R U P A 2
C19' C 0.342(3) 0.978(3) 0.1809(17) 0.120(4) Uani 0.4 1 d D U P A 2
H19D H 0.4100 0.9439 0.2403 0.179 Uiso 0.4 1 calc R U P A 2
H19E H 0.3614 1.0677 0.1591 0.179 Uiso 0.4 1 calc R U P A 2
H19F H 0.3332 0.9237 0.1068 0.179 Uiso 0.4 1 calc R U P A 2
C20 C 0.8319(4) 0.9929(5) 0.4542(5) 0.0673(12) Uani 1 1 d . . . . .
C21 C 0.8503(6) 1.0975(6) 0.5574(7) 0.0904(18) Uani 1 1 d . . . . .
H21A H 0.8149 1.0658 0.6296 0.136 Uiso 1 1 calc R U . . .
H21B H 0.8083 1.1782 0.5278 0.136 Uiso 1 1 calc R U . . .
H21C H 0.9394 1.1144 0.5798 0.136 Uiso 1 1 calc R U . . .
C22 C 0.8862(5) 0.8579(6) 0.4987(7) 0.0898(19) Uani 1 1 d . . . . .
H22A H 0.9771 0.8634 0.5142 0.135 Uiso 1 1 calc R U . . .
H22B H 0.8618 0.7923 0.4353 0.135 Uiso 1 1 calc R U . . .
H22C H 0.8537 0.8333 0.5748 0.135 Uiso 1 1 calc R U . . .
C23 C 0.8844(6) 1.0395(7) 0.3351(7) 0.114(2) Uani 1 1 d . . . . .
H23A H 0.9730 1.0601 0.3550 0.170 Uiso 1 1 calc R U . . .
H23B H 0.8392 1.1174 0.3027 0.170 Uiso 1 1 calc R U . . .
H23C H 0.8737 0.9701 0.2732 0.170 Uiso 1 1 calc R U . . .
H1A H 0.613(4) 0.835(5) 0.546(4) 0.057(13) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.477(3) . ?
S1 N1 1.638(4) . ?
S1 C20 1.826(5) . ?
F1 C9 1.384(5) . ?
N1 C10 1.459(5) . ?
N1 H1A 0.90(5) . ?
O1 C17 1.199(6) . ?
O2 C17 1.301(6) . ?
O2 C18 1.492(17) . ?
O2 C18' 1.57(2) . ?
C1 C6 1.387(7) . ?
C1 C2 1.387(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(6) . ?
C7 C8 1.315(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.492(6) . ?
C8 H8 0.9300 . ?
C9 C17 1.532(6) . ?
C9 C10 1.542(6) . ?
C10 C11 1.512(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.369(6) . ?
C11 C16 1.372(6) . ?
C12 C13 1.369(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.345(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18' C19' 1.49(2) . ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
C20 C21 1.521(8) . ?
C20 C22 1.526(7) . ?
C20 C23 1.534(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 107.1(2) . . ?
O3 S1 C20 105.3(2) . . ?
N1 S1 C20 101.4(2) . . ?
C10 N1 S1 122.3(3) . . ?
C10 N1 H1A 117(3) . . ?
S1 N1 H1A 116(3) . . ?
C17 O2 C18 121.0(8) . . ?
C17 O2 C18' 107.9(13) . . ?
C6 C1 C2 120.7(7) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 C7 121.9(4) . . ?
C1 C6 C7 119.5(5) . . ?
C8 C7 C6 125.9(5) . . ?
C8 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
C7 C8 C9 125.6(4) . . ?
C7 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
F1 C9 C8 109.4(3) . . ?
F1 C9 C17 109.7(3) . . ?
C8 C9 C17 107.2(3) . . ?
F1 C9 C10 107.5(3) . . ?
C8 C9 C10 112.6(3) . . ?
C17 C9 C10 110.3(3) . . ?
N1 C10 C11 111.8(3) . . ?
N1 C10 C9 111.0(3) . . ?
C11 C10 C9 111.2(3) . . ?
N1 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C12 C11 C16 118.4(4) . . ?
C12 C11 C10 120.1(4) . . ?
C16 C11 C10 121.4(4) . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.2(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O1 C17 O2 126.7(4) . . ?
O1 C17 C9 120.1(4) . . ?
O2 C17 C9 113.2(4) . . ?
C19 C18 O2 115.9(15) . . ?
C19 C18 H18A 108.3 . . ?
O2 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
O2 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C19' C18' O2 87.0(15) . . ?
C19' C18' H18C 114.2 . . ?
O2 C18' H18C 114.2 . . ?
C19' C18' H18D 114.2 . . ?
O2 C18' H18D 114.2 . . ?
H18C C18' H18D 111.3 . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C21 C20 C22 112.3(5) . . ?
C21 C20 C23 111.8(5) . . ?
C22 C20 C23 111.7(5) . . ?
C21 C20 S1 106.7(3) . . ?
C22 C20 S1 109.7(3) . . ?
C23 C20 S1 104.2(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C10 -134.1(4) . . . . ?
C20 S1 N1 C10 115.8(4) . . . . ?
C6 C1 C2 C3 -0.4(10) . . . . ?
C1 C2 C3 C4 0.0(11) . . . . ?
C2 C3 C4 C5 0.0(12) . . . . ?
C3 C4 C5 C6 0.3(10) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C5 C6 C7 176.1(5) . . . . ?
C2 C1 C6 C5 0.7(8) . . . . ?
C2 C1 C6 C7 -176.1(5) . . . . ?
C5 C6 C7 C8 -15.0(7) . . . . ?
C1 C6 C7 C8 161.8(5) . . . . ?
C6 C7 C8 C9 -179.7(4) . . . . ?
C7 C8 C9 F1 -1.8(6) . . . . ?
C7 C8 C9 C17 117.1(4) . . . . ?
C7 C8 C9 C10 -121.4(4) . . . . ?
S1 N1 C10 C11 -141.0(3) . . . . ?
S1 N1 C10 C9 94.2(4) . . . . ?
F1 C9 C10 N1 50.6(4) . . . . ?
C8 C9 C10 N1 171.3(3) . . . . ?
C17 C9 C10 N1 -69.0(4) . . . . ?
F1 C9 C10 C11 -74.5(4) . . . . ?
C8 C9 C10 C11 46.2(5) . . . . ?
C17 C9 C10 C11 165.9(4) . . . . ?
N1 C10 C11 C12 136.5(4) . . . . ?
C9 C10 C11 C12 -98.8(4) . . . . ?
N1 C10 C11 C16 -46.6(5) . . . . ?
C9 C10 C11 C16 78.1(5) . . . . ?
C16 C11 C12 C13 0.9(7) . . . . ?
C10 C11 C12 C13 177.9(5) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C12 C11 C16 C15 -0.5(7) . . . . ?
C10 C11 C16 C15 -177.5(4) . . . . ?
C14 C15 C16 C11 0.4(8) . . . . ?
C18 O2 C17 O1 -3.2(13) . . . . ?
C18' O2 C17 O1 -14.5(13) . . . . ?
C18 O2 C17 C9 174.3(10) . . . . ?
C18' O2 C17 C9 162.9(12) . . . . ?
F1 C9 C17 O1 -176.9(4) . . . . ?
C8 C9 C17 O1 64.3(5) . . . . ?
C10 C9 C17 O1 -58.6(5) . . . . ?
F1 C9 C17 O2 5.5(5) . . . . ?
C8 C9 C17 O2 -113.3(4) . . . . ?
C10 C9 C17 O2 123.8(4) . . . . ?
C17 O2 C18 C19 79.8(14) . . . . ?
C18' O2 C18 C19 121(8) . . . . ?
C17 O2 C18' C19' 89.4(13) . . . . ?
C18 O2 C18' C19' -55(7) . . . . ?
O3 S1 C20 C21 -174.8(4) . . . . ?
N1 S1 C20 C21 -63.4(4) . . . . ?
O3 S1 C20 C22 -53.0(4) . . . . ?
N1 S1 C20 C22 58.5(4) . . . . ?
O3 S1 C20 C23 66.8(4) . . . . ?
N1 S1 C20 C23 178.2(4) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd16148
_database_code_depnum_ccdc_archive 'CCDC 1473544'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H26 F N O3 S'
_chemical_formula_weight         343.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6078(18)
_cell_length_b                   18.110(4)
_cell_length_c                   21.537(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3747.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3022
_cell_measurement_theta_min      4.799
_cell_measurement_theta_max      40.732

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21644
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.891
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6964
_reflns_number_gt                4759
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1638 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6964
_refine_ls_number_parameters     433
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.84964(12) 0.11614(6) 0.22340(6) 0.0575(3) Uani 1 1 d . . . . .
S2 S 0.03207(12) -0.08658(6) 0.38012(6) 0.0587(3) Uani 1 1 d . . . . .
F1 F 0.5318(3) 0.13783(12) 0.23235(12) 0.0672(7) Uani 1 1 d . . . . .
F2 F 0.2688(3) -0.02650(14) 0.46867(13) 0.0785(8) Uani 1 1 d . . . . .
N1 N 0.8045(4) 0.20345(19) 0.21369(19) 0.0565(9) Uani 1 1 d D . . . .
N2 N 0.0583(4) 0.00295(18) 0.36860(16) 0.0495(9) Uani 1 1 d D . . . .
O1 O 0.4353(4) 0.3187(2) 0.2640(2) 0.0897(12) Uani 1 1 d . . . . .
O2 O 0.3242(3) 0.21155(18) 0.26471(16) 0.0723(9) Uani 1 1 d . . . . .
O3 O 0.9657(3) 0.10920(16) 0.26859(14) 0.0668(8) Uani 1 1 d . . . . .
O4 O 0.3590(5) 0.1556(2) 0.4308(2) 0.1033(14) Uani 1 1 d . . . . .
O5 O 0.4578(4) 0.0661(2) 0.48593(17) 0.0879(11) Uani 1 1 d . . . . .
O6 O 0.0721(4) -0.13292(18) 0.32603(19) 0.0943(12) Uani 1 1 d . . . . .
C1 C 0.5963(5) 0.2844(3) 0.1220(3) 0.0725(14) Uani 1 1 d . . . . .
H1 H 0.6513 0.3168 0.1448 0.087 Uiso 1 1 calc R U . . .
C2 C 0.5767(6) 0.2961(3) 0.0594(3) 0.0880(17) Uani 1 1 d . . . . .
H2 H 0.6175 0.3364 0.0399 0.106 Uiso 1 1 calc R U . . .
C3 C 0.4962(8) 0.2474(4) 0.0260(3) 0.0933(19) Uani 1 1 d . . . . .
H3 H 0.4831 0.2551 -0.0163 0.112 Uiso 1 1 calc R U . . .
C4 C 0.4362(7) 0.1890(3) 0.0536(3) 0.0875(17) Uani 1 1 d . . . . .
H4 H 0.3827 0.1564 0.0303 0.105 Uiso 1 1 calc R U . . .
C5 C 0.4539(5) 0.1774(3) 0.1168(2) 0.0668(12) Uani 1 1 d . . . . .
H5 H 0.4111 0.1374 0.1360 0.080 Uiso 1 1 calc R U . . .
C6 C 0.5351(5) 0.2251(2) 0.1512(2) 0.0546(11) Uani 1 1 d . . . . .
C7 C 0.5497(4) 0.2130(2) 0.2209(2) 0.0537(10) Uani 1 1 d . . . . .
C8 C 0.6893(5) 0.2358(2) 0.2491(2) 0.0565(12) Uani 1 1 d . . . . .
H8 H 0.6966 0.2896 0.2448 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6950(5) 0.2183(3) 0.3191(2) 0.0791(15) Uani 1 1 d . . . . .
H9A H 0.6112 0.2372 0.3385 0.095 Uiso 1 1 calc R U . . .
H9B H 0.6955 0.1651 0.3244 0.095 Uiso 1 1 calc R U . . .
C10 C 0.8202(7) 0.2503(4) 0.3522(3) 0.109(2) Uani 1 1 d . . . . .
H10A H 0.8169 0.2342 0.3951 0.130 Uiso 1 1 calc R U . . .
H10B H 0.9031 0.2289 0.3338 0.130 Uiso 1 1 calc R U . . .
C11 C 0.8361(10) 0.3282(4) 0.3519(4) 0.161(4) Uani 1 1 d . . . . .
H11A H 0.8529 0.3448 0.3102 0.241 Uiso 1 1 calc R U . . .
H11B H 0.9134 0.3416 0.3778 0.241 Uiso 1 1 calc R U . . .
H11C H 0.7528 0.3508 0.3675 0.241 Uiso 1 1 calc R U . . .
C12 C 0.4317(5) 0.2541(3) 0.2528(2) 0.0595(12) Uani 1 1 d . . . . .
C13 C 0.2059(5) 0.2463(3) 0.2940(3) 0.0865(17) Uani 1 1 d . . . . .
H13A H 0.2300 0.2603 0.3356 0.130 Uiso 1 1 calc R U . . .
H13B H 0.1293 0.2123 0.2950 0.130 Uiso 1 1 calc R U . . .
H13C H 0.1798 0.2894 0.2709 0.130 Uiso 1 1 calc R U . . .
C14 C 0.9296(5) 0.0982(3) 0.1465(2) 0.0675(13) Uani 1 1 d . . . . .
C15 C 0.8220(6) 0.1102(3) 0.0968(2) 0.0947(19) Uani 1 1 d . . . . .
H15A H 0.7980 0.1616 0.0951 0.142 Uiso 1 1 calc R U . . .
H15B H 0.7405 0.0817 0.1062 0.142 Uiso 1 1 calc R U . . .
H15C H 0.8590 0.0949 0.0575 0.142 Uiso 1 1 calc R U . . .
C16 C 0.9693(8) 0.0158(3) 0.1505(3) 0.108(2) Uani 1 1 d . . . . .
H16A H 1.0221 0.0022 0.1144 0.162 Uiso 1 1 calc R U . . .
H16B H 0.8863 -0.0136 0.1525 0.162 Uiso 1 1 calc R U . . .
H16C H 1.0243 0.0074 0.1870 0.162 Uiso 1 1 calc R U . . .
C17 C 1.0564(6) 0.1464(4) 0.1384(3) 0.100(2) Uani 1 1 d . . . . .
H17A H 1.1008 0.1348 0.0997 0.149 Uiso 1 1 calc R U . . .
H17B H 1.1202 0.1376 0.1720 0.149 Uiso 1 1 calc R U . . .
H17C H 1.0290 0.1973 0.1385 0.149 Uiso 1 1 calc R U . . .
C18 C 0.0765(7) 0.0356(4) 0.5406(3) 0.0924(18) Uani 1 1 d . . . . .
H18 H 0.1167 -0.0096 0.5505 0.111 Uiso 1 1 calc R U . . .
C19 C -0.0256(9) 0.0660(6) 0.5785(3) 0.131(3) Uani 1 1 d . . . . .
H19 H -0.0544 0.0402 0.6136 0.157 Uiso 1 1 calc R U . . .
C20 C -0.0839(9) 0.1321(6) 0.5658(4) 0.135(3) Uani 1 1 d . . . . .
H20 H -0.1503 0.1525 0.5921 0.162 Uiso 1 1 calc R U . . .
C21 C -0.0440(9) 0.1674(4) 0.5145(4) 0.121(2) Uani 1 1 d . . . . .
H21 H -0.0847 0.2127 0.5052 0.145 Uiso 1 1 calc R U . . .
C22 C 0.0551(7) 0.1396(3) 0.4750(3) 0.0929(18) Uani 1 1 d . . . . .
H22 H 0.0800 0.1656 0.4394 0.112 Uiso 1 1 calc R U . . .
C23 C 0.1171(5) 0.0730(3) 0.4882(2) 0.0620(12) Uani 1 1 d . . . . .
C24 C 0.2303(5) 0.0436(2) 0.4471(2) 0.0582(12) Uani 1 1 d . . . . .
C25 C 0.1946(4) 0.0371(2) 0.3784(2) 0.0537(10) Uani 1 1 d . . . . .
H25 H 0.1848 0.0880 0.3636 0.064 Uiso 1 1 calc R U . . .
C26 C 0.3117(5) 0.0038(3) 0.3398(2) 0.0700(13) Uani 1 1 d . . . . .
H26A H 0.3231 -0.0477 0.3511 0.084 Uiso 1 1 calc R U . . .
H26B H 0.3979 0.0292 0.3494 0.084 Uiso 1 1 calc R U . . .
C27 C 0.2844(6) 0.0091(3) 0.2702(3) 0.0817(15) Uani 1 1 d . . . . .
H27A H 0.1985 -0.0167 0.2607 0.098 Uiso 1 1 calc R U . . .
H27B H 0.2714 0.0606 0.2592 0.098 Uiso 1 1 calc R U . . .
C28 C 0.3973(7) -0.0220(3) 0.2313(3) 0.102(2) Uani 1 1 d . . . . .
H28A H 0.4825 0.0040 0.2395 0.153 Uiso 1 1 calc R U . . .
H28B H 0.3735 -0.0166 0.1882 0.153 Uiso 1 1 calc R U . . .
H28C H 0.4091 -0.0733 0.2408 0.153 Uiso 1 1 calc R U . . .
C29 C 0.3596(6) 0.0959(3) 0.4527(2) 0.0691(13) Uani 1 1 d . . . . .
C30 C 0.5797(6) 0.1142(4) 0.4934(3) 0.115(2) Uani 1 1 d . . . . .
H30A H 0.6167 0.1263 0.4533 0.172 Uiso 1 1 calc R U . . .
H30B H 0.6494 0.0890 0.5173 0.172 Uiso 1 1 calc R U . . .
H30C H 0.5527 0.1586 0.5145 0.172 Uiso 1 1 calc R U . . .
C31 C -0.1599(5) -0.0829(2) 0.3787(2) 0.0606(11) Uani 1 1 d . . . . .
C32 C -0.2051(7) -0.0376(4) 0.4336(3) 0.128(3) Uani 1 1 d . . . . .
H32A H -0.1901 0.0138 0.4250 0.192 Uiso 1 1 calc R U . . .
H32B H -0.1518 -0.0516 0.4694 0.192 Uiso 1 1 calc R U . . .
H32C H -0.3021 -0.0460 0.4415 0.192 Uiso 1 1 calc R U . . .
C33 C -0.2108(6) -0.0538(3) 0.3177(3) 0.105(2) Uani 1 1 d . . . . .
H33A H -0.3069 -0.0669 0.3122 0.158 Uiso 1 1 calc R U . . .
H33B H -0.1566 -0.0748 0.2846 0.158 Uiso 1 1 calc R U . . .
H33C H -0.2015 -0.0010 0.3170 0.158 Uiso 1 1 calc R U . . .
C34 C -0.2042(6) -0.1632(3) 0.3859(3) 0.0943(19) Uani 1 1 d . . . . .
H34A H -0.3039 -0.1661 0.3868 0.141 Uiso 1 1 calc R U . . .
H34B H -0.1670 -0.1827 0.4239 0.141 Uiso 1 1 calc R U . . .
H34C H -0.1695 -0.1914 0.3515 0.141 Uiso 1 1 calc R U . . .
H2A H 0.022(4) 0.019(2) 0.3357(13) 0.046(12) Uiso 1 1 d D . . . .
H1A H 0.863(4) 0.232(2) 0.1991(19) 0.056(14) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.486(3) . ?
S1 N1 1.653(4) . ?
S1 C14 1.853(5) . ?
S2 O6 1.486(4) . ?
S2 N2 1.659(3) . ?
S2 C31 1.846(5) . ?
F1 C7 1.394(4) . ?
F2 C24 1.401(5) . ?
N1 C8 1.466(6) . ?
N1 H1A 0.82(2) . ?
N2 C25 1.463(5) . ?
N2 H2A 0.84(2) . ?
O1 C12 1.195(5) . ?
O2 C12 1.314(5) . ?
O2 C13 1.444(6) . ?
O4 C29 1.178(6) . ?
O5 C29 1.301(6) . ?
O5 C30 1.468(7) . ?
C1 C6 1.375(6) . ?
C1 C2 1.379(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.343(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.524(6) . ?
C7 C12 1.520(6) . ?
C7 C8 1.529(6) . ?
C8 C9 1.542(6) . ?
C8 H8 0.9800 . ?
C9 C10 1.514(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.418(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.504(7) . ?
C14 C17 1.508(7) . ?
C14 C16 1.544(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.372(7) . ?
C18 C19 1.391(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.349(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.332(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.500(7) . ?
C24 C25 1.524(6) . ?
C24 C29 1.567(7) . ?
C25 C26 1.524(6) . ?
C25 H25 0.9800 . ?
C26 C27 1.526(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.482(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C33 1.499(7) . ?
C31 C32 1.503(7) . ?
C31 C34 1.523(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 111.15(19) . . ?
O3 S1 C14 105.0(2) . . ?
N1 S1 C14 99.4(2) . . ?
O6 S2 N2 113.3(2) . . ?
O6 S2 C31 105.4(2) . . ?
N2 S2 C31 96.55(19) . . ?
C8 N1 S1 121.0(3) . . ?
C8 N1 H1A 117(3) . . ?
S1 N1 H1A 118(3) . . ?
C25 N2 S2 121.8(3) . . ?
C25 N2 H2A 110(3) . . ?
S2 N2 H2A 114(3) . . ?
C12 O2 C13 116.6(4) . . ?
C29 O5 C30 113.1(5) . . ?
C6 C1 C2 120.5(5) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 C7 121.5(4) . . ?
C5 C6 C7 119.3(4) . . ?
F1 C7 C12 107.9(3) . . ?
F1 C7 C6 107.7(3) . . ?
C12 C7 C6 107.8(3) . . ?
F1 C7 C8 107.6(3) . . ?
C12 C7 C8 110.0(4) . . ?
C6 C7 C8 115.6(4) . . ?
N1 C8 C7 110.4(4) . . ?
N1 C8 C9 113.5(4) . . ?
C7 C8 C9 111.3(4) . . ?
N1 C8 H8 107.1 . . ?
C7 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C10 C9 C8 114.2(5) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 117.7(6) . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
C9 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 123.9(5) . . ?
O1 C12 C7 123.3(4) . . ?
O2 C12 C7 112.8(4) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C17 112.9(5) . . ?
C15 C14 C16 110.4(4) . . ?
C17 C14 C16 111.4(5) . . ?
C15 C14 S1 109.0(4) . . ?
C17 C14 S1 109.7(3) . . ?
C16 C14 S1 102.9(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.2(6) . . ?
C23 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 121.6(8) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C21 C20 C19 118.4(8) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 122.5(8) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C21 C22 C23 119.6(7) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 118.7(5) . . ?
C18 C23 C24 121.0(5) . . ?
C22 C23 C24 120.3(5) . . ?
F2 C24 C23 108.6(4) . . ?
F2 C24 C25 108.1(3) . . ?
C23 C24 C25 115.9(4) . . ?
F2 C24 C29 108.3(4) . . ?
C23 C24 C29 108.4(4) . . ?
C25 C24 C29 107.4(4) . . ?
N2 C25 C26 114.5(3) . . ?
N2 C25 C24 112.0(4) . . ?
C26 C25 C24 113.2(4) . . ?
N2 C25 H25 105.4 . . ?
C26 C25 H25 105.4 . . ?
C24 C25 H25 105.4 . . ?
C25 C26 C27 112.6(4) . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C28 C27 C26 113.9(5) . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O4 C29 O5 127.1(5) . . ?
O4 C29 C24 121.3(5) . . ?
O5 C29 C24 111.5(5) . . ?
O5 C30 H30A 109.5 . . ?
O5 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O5 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C33 C31 C32 113.8(5) . . ?
C33 C31 C34 109.5(4) . . ?
C32 C31 C34 111.2(5) . . ?
C33 C31 S2 110.7(4) . . ?
C32 C31 S2 107.2(4) . . ?
C34 C31 S2 104.1(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C8 -95.3(4) . . . . ?
C14 S1 N1 C8 154.4(3) . . . . ?
O6 S2 N2 C25 -83.6(4) . . . . ?
C31 S2 N2 C25 166.5(3) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C2 C1 C6 C7 -177.1(5) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
C1 C6 C7 F1 -155.1(4) . . . . ?
C5 C6 C7 F1 27.7(5) . . . . ?
C1 C6 C7 C12 88.7(5) . . . . ?
C5 C6 C7 C12 -88.5(5) . . . . ?
C1 C6 C7 C8 -34.8(6) . . . . ?
C5 C6 C7 C8 148.0(4) . . . . ?
S1 N1 C8 C7 -78.7(4) . . . . ?
S1 N1 C8 C9 47.1(5) . . . . ?
F1 C7 C8 N1 69.6(4) . . . . ?
C12 C7 C8 N1 -173.1(4) . . . . ?
C6 C7 C8 N1 -50.7(5) . . . . ?
F1 C7 C8 C9 -57.3(5) . . . . ?
C12 C7 C8 C9 60.0(5) . . . . ?
C6 C7 C8 C9 -177.7(4) . . . . ?
N1 C8 C9 C10 64.1(6) . . . . ?
C7 C8 C9 C10 -170.7(4) . . . . ?
C8 C9 C10 C11 60.7(8) . . . . ?
C13 O2 C12 O1 -1.0(7) . . . . ?
C13 O2 C12 C7 -178.9(4) . . . . ?
F1 C7 C12 O1 161.7(4) . . . . ?
C6 C7 C12 O1 -82.2(5) . . . . ?
C8 C7 C12 O1 44.6(6) . . . . ?
F1 C7 C12 O2 -20.3(5) . . . . ?
C6 C7 C12 O2 95.7(4) . . . . ?
C8 C7 C12 O2 -137.4(4) . . . . ?
O3 S1 C14 C15 -175.4(4) . . . . ?
N1 S1 C14 C15 -60.4(4) . . . . ?
O3 S1 C14 C17 -51.2(4) . . . . ?
N1 S1 C14 C17 63.8(4) . . . . ?
O3 S1 C14 C16 67.4(4) . . . . ?
N1 S1 C14 C16 -177.5(4) . . . . ?
C23 C18 C19 C20 -1.2(10) . . . . ?
C18 C19 C20 C21 1.7(12) . . . . ?
C19 C20 C21 C22 -0.9(13) . . . . ?
C20 C21 C22 C23 -0.4(11) . . . . ?
C19 C18 C23 C22 -0.1(8) . . . . ?
C19 C18 C23 C24 177.8(5) . . . . ?
C21 C22 C23 C18 0.9(8) . . . . ?
C21 C22 C23 C24 -177.0(5) . . . . ?
C18 C23 C24 F2 5.8(6) . . . . ?
C22 C23 C24 F2 -176.3(4) . . . . ?
C18 C23 C24 C25 127.6(5) . . . . ?
C22 C23 C24 C25 -54.5(6) . . . . ?
C18 C23 C24 C29 -111.6(5) . . . . ?
C22 C23 C24 C29 66.3(6) . . . . ?
S2 N2 C25 C26 57.9(5) . . . . ?
S2 N2 C25 C24 -72.8(4) . . . . ?
F2 C24 C25 N2 75.9(4) . . . . ?
C23 C24 C25 N2 -46.2(5) . . . . ?
C29 C24 C25 N2 -167.5(4) . . . . ?
F2 C24 C25 C26 -55.5(5) . . . . ?
C23 C24 C25 C26 -177.6(4) . . . . ?
C29 C24 C25 C26 61.1(5) . . . . ?
N2 C25 C26 C27 59.3(6) . . . . ?
C24 C25 C26 C27 -170.6(4) . . . . ?
C25 C26 C27 C28 179.3(4) . . . . ?
C30 O5 C29 O4 -2.2(8) . . . . ?
C30 O5 C29 C24 -178.7(4) . . . . ?
F2 C24 C29 O4 171.0(5) . . . . ?
C23 C24 C29 O4 -71.4(6) . . . . ?
C25 C24 C29 O4 54.5(6) . . . . ?
F2 C24 C29 O5 -12.3(6) . . . . ?
C23 C24 C29 O5 105.3(5) . . . . ?
C25 C24 C29 O5 -128.8(4) . . . . ?
O6 S2 C31 C33 -56.5(4) . . . . ?
N2 S2 C31 C33 59.9(4) . . . . ?
O6 S2 C31 C32 178.9(4) . . . . ?
N2 S2 C31 C32 -64.7(4) . . . . ?
O6 S2 C31 C34 61.1(4) . . . . ?
N2 S2 C31 C34 177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13B O3 0.96 2.51 3.433(7) 162.6 1_455
C33 H33B O6 0.96 2.59 3.078(7) 111.5 .
C33 H33C S1 0.96 2.97 3.732(5) 137.5 1_455
N2 H2A O3 0.84(2) 2.24(3) 3.022(4) 154(3) 1_455
N1 H1A O6 0.82(2) 2.59(3) 3.304(5) 147(4) 3_655

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

